Have We Met?
by itsronia
Summary: Elena Gilbert is an aspiring journalist who moved to New York to make all her dreams true with her two best friends Caroline and Bonnie. She's been dating a swanky New York bachelor, Stefan Salvatore for two months and things are going great. Until she meets his brother Damon for the first time. Or so she thought…and her world gets tipped upside down. AU/AH
1. Chapter 1

**ELENA'S POV:**

Elena tapped her feet in anticipation as she waited for her boyfriend to emerge from the front door.

"Stefan," she called glancing at her watch. "We're going to be late if you don't hurry up!"

They were on their way to the Salvatore family reunion.

Who were the Salvatores? Well the answer was, probably the richest family in New York. Maybe even in America. The world.

And Elena's boyfriend, Stefan was right in the midst of that. His parents owned the family oil business and he would inherit half the empire when they died.

They really couldn't afford to be late.

"Okay, okay I'm here," Stefan said as he walked out of the house. "And by the way, you look fantastic." He kissed her on the cheek.

"So they sent a limo, huh?" Elena remarked casually, even though casual was the last thing she was feeling right now. A limousine?  
Stefan rolled his eyes. "Yes, the Salvatores can tend to be ridiculously over the top and ostentatious. But what the hell? Let's live a little."

They got into the waiting limo, and started their journey to the Salvatore mansion.

Elena found herself running through scenarios of things to say, but she racked her brain and found nothing. Her mind was occupied with other things.

"You've been awfully quiet," Stefan remarked as the silence in the car permeated. "Are you nervous?" he teased.

Elena gulped slightly in her throat. In actual fact, she was nervous. Like really nervous. She hadn't met the parents and family of anyone she's been dating since her old high school boyfriend Matt. And that technically didn't count because she basically grew up with them, being family friends for ages.

Meeting the parents. It's a big step. Were they ready?

Well it was too late to change her mind.

"I'm fine," Elena stated with a poised smile.

Because that's who she was. In her group of best friends, Caroline was the crazy, bubbly and fun one; Bonnie was the funny, smart and intelligent one and she was the poised, elegant, albeit slightly boring one.

"So tell me about your family," Elena remarked as she glanced over at Stefan. "Well your immediate family that is."

He hadn't really told her anything about them. The only things she knew were tidbits from the many news articles about the Salvatores. And there were a lot of them; their family was wide and extensive.

"Well to be truthful, my dad's a judgemental asshole; my mother's hates every woman I've ever dated," Stefan stated with a dry smile.

Elena's stomach lurched. Wow, that really helped her with her nerves.

"Oh and my brother is the dark horse of the family. He's a notorious womaniser, isn't seen in public that much anymore and can be a real jerk."

"Sounds delightful," Elena stated with a shaky grin.

She really wasn't sure why she was so nervous. She always made a good impression on parents. However this was different.

"Come on you're not actually worried are you?" Stefan laughed.  
"Well it's intimidating! Your family is one of the wealthiest and influential families in New York. I'm from Mystic Falls," Elena said in a rush. "What if they think I'm some country hick?"

"Well I think you're one of the most sexy and sophisticated women I've ever met," Stefan said matter of factly.

Elena rolled her eyes playfully. "Well I guess that's a good sign. You're not your parents though."

"I think I can make a pretty good judgement myself," Stefan said as he kissed her gently on the lips.

They chatted amiably until they arrived at Stefan's parents' house.

Elena stepped out of the limo and her jaw dropped. This house was amazing. In fact, it couldn't even be described as a house, it was well and truly a mansion. It simply smacked of wealth.

"Shall we?" Stefan asked as he offered his arm to her.

The butlers, yes multiple butlers, welcomed them in and took their coats. As they headed down into the extensive party, Stefan leant in and whispered soothingly in Elena's ear, "You'll be wonderful."

Her nerves were smoothed down and she felt that she was ready to face the lions.

The lions being Giuseppe and Lily Salvatore of course.

* * *

As soon as they entered into the party, a voice called out to them.

"Stefan darling!"

It was Lily Salvatore. And with her, her husband. Stefan's parents.

Elena got a few seconds to quickly take them in. She was dressed elegantly in a white pantsuit, with a glittering diamond necklace that obviously was all too real. He was wearing a simple black suit, tailored within an inch of its life.

"Mum, Dad this is Elena. Elena this is Giuseppe and Lily Salvatore."

"It's a pleasure to meet you," Elena said smoothly as she shook first Giuseppe's hand and then Lily's. The handshake was a vital part of meeting the parents. It was one of the first impressions. She had to make sure not to shake too hard, otherwise she'd seem aggressive, or too soft, otherwise she'd seem like she was afraid.

She could feel both their eyes appraising her up and down, and she shivered slightly. Their reputation sure preceded them.

"I've heard so much about you Elena," Lily said calmly. "I feel like I know you already. Stefan won't stop talking about you."

Elena felt herself begin to relax slightly at the sign of that. Lily's words were delivered without a trace of warmth but at least the words coming out were nice. She squeezed Stefan's hand as they continued to converse.

"So where are you from?" Lily enquired.

"Mystic Falls, it's a small town in Virginia. I grew up there," Elena said with a small smile on her face. She always felt happier when talking about her hometown, even though there were some unhappy memories always lingering.

"And what brought you to New York?" Giuseppe asked.

"Well it's always been an ambition of mine to become a journalist, so I'm currently studying journalism part time at NYU."

Giuseppe frowned slightly. "Journalism?"

"Dad doesn't like journalists," Stefan whispered.

"Damn straight I don't. They're interfering nobodies who have no business prying into other people's private lives! That's what journalists are!"

"Well that's great for me," Elena muttered under her breath.

"Pardon?"

"Oh nothing," Elena replied hastily. She made a mental note not to bring up the subject again.

"So what do you do now, apart from the part-time studying, Elena?" Lily asked.

"I run a bar," Elena said with an engaging smile.

Any sign of a smile quickly disappeared from Stefan's parents.

"I co-own it with my friend Enzo. He deals with the money part of the business, and I do the customer part, making drinks and all that."

Lily and Giuseppe looked at each other quickly.

"So you're a bartender?" Lily queried. "That's…interesting."

"Elena co-owns a business, Mum," Stefan said defending her. "She's not just a bartender."

Elena felt a small rush of warmth for him sticking up for her.

"Well it's not really a profession for a lady," Lily articulated with a hint of disapproval. "Bartender or not."

"I totally agree," Elena said quickly. "I'm looking for a job in something else once I finish my degree at NYU."

"Oh? What jobs are you looking at?" Lily asked.

Elena winced a little, having to bring up the subject again. "Just anything in journalism. I'd love to work for _The New York Times_ , that's always been a dream of mine."

"That's nice dear," Lily said noncommittally "Much more appropriate than bartending for sure."

Elena nodded, not sure what else to do.

Lily glanced over to her husband as a silent signal passed between them that Elena couldn't interpret.

"Well we're going to go," Giuseppe said smoothly. "We've got many people to welcome. It was a pleasure meeting you Elena."

"Yes it certainly was," Lily added. They turned their heel and disappeared into the party.

"Well, that went terrible," Elena said wryly.

Stefan looked at her. "Well…I wouldn't say terrible."

"I'm sorry were you not present for that whole conversation? Your dad hates journalists and your mum hates bartenders. I'm literally the two things your parents hate. Yippee."

"Well, I don't hate you," Stefan matter of factly. "I definitely like you."

"I know you like me. I just wanted them to."

Stefan sighed. "They never like anyone, and honestly it really didn't go that badly. When they met my old girlfriend Gina, Lily called her a gold digger and a man-eater. So compared to that, you're in the clear."

Elena smiled a bit at that anecdote. She was here for Stefan after all, so what if his parents didn't really like her?

"Anyway, is there anymore relatives I have to meet?" Elena asked. "Not that it hasn't been a pleasure so far."

"There's my Uncle Herb, and my Aunt Joan, they love picking apart people, and my cousin in law Glen, my niece Rhonda of course, funnily enough she's older than me and my…" Stefan trailed off as he saw the look of horror on Elena's face. "I'm kidding Elena. We're off the hook for the night."

She breathed a sign of relief. That would've been a lot of mindless chitchat.

"Unless Uncle Herb comes by," Stefan added with a grin. "He's always interested in the girls I'm dating. Always up for a chat."

Elena laughed. "Well hopefully Uncle Herb will approve of me."

"Oh, and there's my brother. Damon's always been the successful one of the two of us, so I can't wait to show you off."

"What I'm a prize?"

Stefan smiled steadily. "To me you are."

Elena felt slightly uneasy at that statement. She didn't really want to be anyone's possession, even if it was Stefan Salvatore.

It was just the principle of it.

They mingled for a while and ate some questionable fancy food, including sweetbreads, which Elena found out, wasn't actually a bread that was sweet but the pancreas of an animal. Good times.

They were chatting near the front of the party with some vague business type people when a dark haired man, with intense, piercing blue eyes entered through the front door. "Stefan, my man," he called as he strode over, clapping Stefan on the back.

Elena was distracted by a man who asking her questions about how she ran her bar while Stefan greeted this mystery man.  
She heard the name "Damon" uttered a few times, and realised that this was Stefan's older brother, the dark horse of the family. She then disentangled herself from the quite persistent businessman, and returned her full attention to the two brothers. Knowing it was important to Stefan, she turned on her most charming smile as she turned to face them.

"Damon, this is Elena Gilbert," Stefan said proudly.

Damon's eyes snapped to Elena and his eyes widened.

And for the second time tonight, Elena's jaw dropped.

When she arrived in New York, the very first night, Caroline and Bonnie were off on a double date with two guys they had met at a bar the night before. Elena decided to go to a bar, where she'd met an intense mystery stranger in a drunken haze, who she went home with that night. She'd left early that morning, slightly embarrassed about what happened. She'd never seen him again.

Until now.

The universe really screwed her over this time.

Because the mystery stranger she hooked up with was Damon Salvatore, her boyfriend's brother.

Could life get any worse?

"Anyway, I've got to say hi to Jack, why don't you two get acquainted," Stefan said as he kissed Elena on the cheek quickly and walked off.

"So, Elena is it?" Damon quipped as he winked at her.

Yes, life really could get worse.

* * *

 **Hello! This is my first Vampire Diaries fic.**

 **I'm Delena and Steroline all the way, so there's just be a little bit of Stefan/Elena to set up the story. This is going to be a Delena/Steroline story.**

 **I'm just going to put this on FF to gauge a reaction, so if you liked it please review and I shall continue! If not then I guess this will just be another story I started and never finished, haha. (Sorry if this chapter is a bit short, it's just setting up the story).**


	2. Chapter 2

As soon as Stefan left, Elena dropped her cool and calm façade and whirled around to face Damon.

Damon Salvatore.

Not the mysterious guy she hooked up with the first night she arrived in New York, but the brother of the guy she was currently dating. Life had thrown her a hell of a curveball this time.

"What are you doing here?" Elena hissed as she looked around anxiously to make sure no one was listening.

"What am I doing here? This is my family reunion! The question is what are you doing here?" Damon said indignantly.

"I'm Stefan's girlfriend."

Damon's eyes widened slightly at the mention of the word 'girlfriend'.

"Girlfriend? I'm sorry, girlfriend?" he repeated as a grin spread over his face.

"Yes, girlfriend," Elena replied shortly. She couldn't believe this was actually happening.

"This is going to be a really, really, really fun night." Damon declared.

"And why exactly is it going to be that?" Elena asked.

"Well the wonderful combination of you, Stefan and me of course. Don't you reckon we are a lovely combination, the three of us? We all fit together, like puzzle pieces," he said wickedly.

Elena was slightly taken aback. Clearly he was more eccentric then she had heard, and it showed.

"I'm just joking," Damon added when he saw the expression on her face. "It's just always nice to meet my baby brother's girlfriends, that's all."  
"Really?" Elena questioned. "So there's been a lot, huh?"

"Surprisingly not that many," Damon replied swiftly. "Me? I go through women quicker than him. And you my dear, were lucky enough to be one of them."

Elena rolled her eyes. He seemed more and more like an asshole by the second. Who knew what coerced her into sleeping with him in the first place.

"Champagne?" They both turned around to see a waiter holding a tray of champagne flutes in his hand.

"Tonight, yes," Elena replied swiftly as she took one. She seriously needed something to take the edge of this night. First Stefan's parents taking an instant dislike to her and then finding out that she slept with her boyfriend's brother. It wasn't even eight o'clock yet, and she was already going through hell.

"Sir?"

"Don't mind if I do," Damon said perking up at the sign of alcohol.

They both drained their glasses in a single gulp.

"So…" Elena shifted uncomfortably. "This is pretty awkward."

Damon raised his eyebrows. "It is? I had no idea."

"How is it not awkward and uncomfortable for you?"

"Like this," Damon said as he shrugged his shoulders. "Eh."

"We just drained a glass of champagne in two seconds, doesn't that imply that you feel uncomfortable?" Elena asked.

"Well you obviously haven't spent much time around me, apart from our little dalliance, because you would know that a glass of champagne to Damon Salvatore is nothing."

Elena couldn't help but laugh at the situation a little. It was so ironic that they were discussing champagne when there was a little bit of a family issue surrounding the fact that she had slept with Damon Salvatore, of all people.

"So, Elena. Elena Gilbert," he continued. "The whole 'no names we'll just be strangers from that one night' thing didn't really work out."

And they were back to discussing it.

"I guess not," Elena answered quickly. "Why did we have that rule anyway?"

"As I recall, you were extremely fascinated by my devastating good looks and demeanour and you wanted the experience to be, and I quote, 'an experience we'll remember for a lifetime, no names, no numbers, just sex'. And, it was quite an experience."

Elena blushed slightly at the recollection. "How do you even remember what I 'quoted' from that night? Because, I really doubt I'd say something like that."

"Trust me," he said as he tapped the side of his head with his finger. "I wouldn't just forget something like that."

His eyes burned into her as he said that. Elena tried to avoid his gaze but the intensity in his eyes kept her fixed onto him.

"So…" she said, trying to change the subject. "What do you do?"

"Apart from accidently romance my brother's girlfriends, I help run my father's business," Damon replied offhandedly.

"Oh, that sounds interesting," Elena said lightly. "Tell me more."

"Actually it's ridiculously boring. It's all paperwork and networking, plus Dad doesn't really give a shit what I do, as long as I don't cause any trouble. He's always been more invested in your boyfriend."

"I'm sure that's not true."

"Well I'm sure it is."

Another awkward silence penetrated the air. Elena felt increasingly nervous and whipped around to look for a waiter holding any sort of alcohol.

Not seeing any in her sight, she turned back to Damon. "So… I should go find Stefan." She turned away as to go but was deterred by his hand on gripping her forearm.

"Actually, I have a few questions for you," Damon said with a serious look on his face.

Was he going to grill her about Stefan? Maybe he cared about his little brother and wanted to look out for him. Maybe he wanted to find out that she wasn't just some gold digging whore.

"Which one of the Salvatore men is better in bed?"

Nope, that obviously wasn't it. "Damon, don't be so gross," Elena asserted.

"It's serious question Elena," Damon quipped.

"And it's a question I'm not answering."

"Why did you leave so early that morning anyway?" Damon asked. "Couldn't be because I was bad in bed, because you and I both know, I am pretty great."

Elena rolled her eyes. "Firstly, I had to work. And secondly, don't flatter yourself. I've had better."

"Oh? Would that be my baby brother Stefan? Maybe he and I could compare notes," Damon smirked.

"I'm not even going to dignify that with a response," Elena said in disgust.  
"Also, Elena, you work at a bar. Those establishments tend to open at a, let's say, later hour then six in the morning. So the "I had work" excuse isn't really feasible in this situation."  
"Haven't you ever heard of a little something called a business meeting?

"Well you didn't have any meetings in your calendar that day," Damon stated.  
"You went through my phone? What the hell?" Elena said strongly.

"It was on the dresser! I woke up in the middle of the night."

"What I don't get is, you say I'm one of many women yet you remember so many vivid details that night? Maybe I'm the one who left the impression," Elena said swiftly as she stared at him.

Damon snorted. "Trust me, no one leaves an impression on me for longer than twenty four hours."

Just then, a man in a suit approached Damon.

"Damon! How are you," he said jovially as he shook Damon's hand.

"Neil, I've never been better," Damon replied with a wicked look in his eye. "This is –"

"I'm going to use the ladies room. Excuse me," Elena said quickly as she left Damon standing there with whoever Neil was.

As she looked back, she saw Damon still watching her. As he caught her eye he winked again.  
As soon as she reached the bathroom, he shut herself in and let out the deep breath she had been holding in in what seemed forever.

Oh. My. God.

The first serious boyfriend she had in forever, was the brother of the guy she had a one-night stand with when she arrived in New York. Was the universe punishing her for something? Did she do something wrong? Was she a horrible person in a past life? And more importantly, what was she going to do about this situation?

She really doubted Stefan would care that much, but still it was possibly the worst position to put him in. He'd made it very clear that him and his brother had a weird competition thing going in work, and life in general.

Elena was stuck for ideas, so naturally she called Bonnie.

She quickly punched the numbers in, praying Bonnie would pick up. She seriously needed some advice.

"Hey Elena! What's up? How's the big family reunion going?"

Elena leaned against the bathroom door. "Literally a disaster."

"What happened?"

"You remember the guy I told you about? From the first night I was here in New York."

"The mysterious hook up? Of course."

"Well, not so mysterious anymore. He's Stefan's brother."

"Oh. This isn't good."

Elena groaned. "No kidding. What the hell am I supposed to do? "

Bonnie deliberated for a second and then arrived at the answer that Elena knew she would. "Tell Stefan."

"I knew I should've called Caroline."

"Come on Elena, it's obvious. You're going to have to tell Stefan at some point. And he'll understand, it's not like you guys were together at the time."

"But he has some weird rivalry thing with his brother. Seriously, they're so competitive. I don't know how Stefan's going to react."

Bonnie sighed. "Elena, what's the golden rule of every relationship?"

"Keep information that could potentially hurt the guy you're dating to yourself?"

"Tell the truth."

"Well I'm not going to spoil the night, I'll tell him the next time I see him."

"I'm telling you Elena, it's not a good idea."  
Elena took a deep breath. "Well I'm going to go with it."

"What if Damon's already told him?"

Elena cursed. "Shit, I didn't think of that."

"So…what are you going to do?" Bonnie asked. "The right thing, or the one that can potentially get you in trouble?"

Elena groaned. "I'll do the right thing."

"Well then why are you still talking to me? Go! Find him!"

"Okay, I'm going. Thanks Bon."

Elena hung up and composed herself. She really should've called Caroline, she thought as she smoothed her hair down in the mirror. Caroline would've told her to forget about it and just go have fun, but now she had to tell Stefan.

Her phone rang and she picked it up without looking at the caller ID, assuming it was Bonnie.

"Bonnie, I'm going to go do it right now, okay?"

"Going to do what?" Caroline's perky voice came through the phone.

"Caroline! I thought you were Bonnie. Anyway since you called…how about you give me some advice?"

"Sure. Hit me."

"So it turns out that Stefan's mystery brother Damon is actually the guy that I had a one night stand with, the night I arrived in New York. And he's also very aware of the fact that I'm his brother's girlfriend. And Stefan and Damon have a weird competitive rivalry thing going. And also, it turns out Damon's also a total jackass who makes horrible innuendos."

Caroline started laughing hysterically.

Elena pursed her lips. It really wasn't that funny. She was in a crisis!  
"Caroline!"

"I'm sorry, I'm sorry, it's just this is the best thing that's happened to me in forever," she replied breaking off into laughter again.  
"Can we get back to the issue please? When I told Bonnie this, she didn't even laugh."

"Um yeah, it's Bonnie. What's new?"

"Can you just tell me what to do please? Bonnie told me to tell him the truth, and she stressed that it should be immediately. And I honestly think it's not a great idea."

"Elena, you're not going to want to hear this but –"

"You're right I don't. Goodbye."

" – you should tell Stefan. What if Damon tells him? Wouldn't you rather he heard that you slept with his brother from you, not him?"

Elena laughed. "Just hearing that sentence reminds me how ridiculous this situation is. There's more than a million people in New York, how the hell did I sleep with Damon Salvatore? And then start dating his borther?"

"You know according to his Wikipedia page, he's supposed to be very attractive."

"Caroline! Did you seriously stalk the Salvatores on Wikipedia of all things?"

"Um, once again, do you know who you're talking to? Of course I did! Also, can you please confirm or deny that Damon Salvatore is very attractive."

"Seriously?"

"Yes. Tell me. Let me live vicariously through you! If he's anything like Stefan, he's got to be ridiculously hot."

"He doesn't look like Stefan, but yes he's attractive. Happy?"  
"Yes, I am."

"Anyway…do you reckon I could wait until the next time I see Stefan to tell him the news? I mean his family reunion should be something to be celebrated and all that, I don't want to spoil it. I'm seeing him for lunch tomorrow, I can just tell him then," Elena explained.  
"I guess waiting a day wouldn't hurt," Caroline said reluctantly. "But you should probably go suss out if Damon has said anything to him yet. Quickly."

"Okay, I'm going. Thanks for the advice."

"No problem let me know how it goes. I want every single juicy detail of tonight when you get back."

Elena hung up the phone. Her talk with Caroline had reassured her slightly, and without the added pressure of having to tell Stefan straightaway, Elena figured she could deal with the whole Damon situation. For now at least.

As she entered the room again, thoughts whirled through her head.

 _What if he's told Stefan already? What if Stefan is mad? What the hell am I going to say to find out if Damon has actually said anything to him?_

She spotted Stefan over the other side of the room, talking animatedly with a tall man, and approached cautiously and tapped Stefan on the arm.

"There you are," Stefan said quickly as he kissed her on the cheek. "Where'd you go?"

"Have you seen Damon?" Elena asked quickly as she swivelled her neck around.

"No…I left him with you," Stefan replied questioningly. "Why?"

"Oh no reason." Elena grabbed Stefan's hand and squeezed it reassuringly. Whether it was to reassure her or Stefan, who knows.

One thing was for sure; this relationship was going to be a rollercoaster ride.

* * *

 **A/N: Hello! I apologise for being so slack with putting up this chapter but I have a good excuse. I graduated! I just returned after two weeks of graduation celebrations at the beach. I'm taking a gap year, so I'm really going to write a lot, which I'm very excited about. Expect much more regular chapters from me! Until next time x**

 **P.S. Thanks for all the lovin on the first chapter!**


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